2020
DOI: 10.1038/s41467-020-14494-8
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Direct C–H difluoromethylation of heterocycles via organic photoredox catalysis

Abstract: The discovery of modern medicine relies on the sustainable development of synthetic methodologies to meet the needs associated with drug molecular design. Heterocycles containing difluoromethyl groups are an emerging but scarcely investigated class of organofluoro molecules with potential applications in pharmaceutical, agricultural and material science. Herein, we developed an organophotocatalytic direct difluoromethylation of heterocycles using O 2 as a green oxidant. The C-H oxidative difluoromethylation ob… Show more

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Cited by 121 publications
(77 citation statements)
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References 64 publications
(68 reference statements)
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“…In the absence of visible light or under white light irradiation, no desired product 3 aa was observed (Table 1, entries 16 and 17). Subsequently, several photocatalysts, including Ru(bpy) 2 Cl 2 , methylene blue, fluorescein, rose bengal and eosin Y, were examined to improve the efficiency of the [c] 390-395 nm CH 3 CN -82 26 [d] 390-395 nm CH 3 CN -Trace 27 [e] 390-395 nm CH 3 CN -71 28 [f] 390-395 nm CH 3 CN -84 29 [g] 390-395 nm CH 3 CN -73 30 [h] 390 Cl 2 ) = 0.77 V versus SCE in acetonitrile, [26] E p/2 (methylene blue) = 1.60 V versus SCE in acetonitrile, [27] E p/2 (fluorescein) = 0.78 V versus SCE in acetonitrile, [28] E p/2 (rose bengal) = 0.99 V versus SCE in acetonitrile, [29] E p/2 (eosin Y) = 0.79 V versus SCE in acetonitrile]. [30] So, the above mentioned photocatalysts cannot react with substrate 1 a (E p/2 = 1.84 V versus SCE in acetonitrile) or 2 a (E p/2 = 1.81 V versus SCE in acetonitrile) via an electron transfer process.…”
Section: Resultsmentioning
confidence: 99%
“…In the absence of visible light or under white light irradiation, no desired product 3 aa was observed (Table 1, entries 16 and 17). Subsequently, several photocatalysts, including Ru(bpy) 2 Cl 2 , methylene blue, fluorescein, rose bengal and eosin Y, were examined to improve the efficiency of the [c] 390-395 nm CH 3 CN -82 26 [d] 390-395 nm CH 3 CN -Trace 27 [e] 390-395 nm CH 3 CN -71 28 [f] 390-395 nm CH 3 CN -84 29 [g] 390-395 nm CH 3 CN -73 30 [h] 390 Cl 2 ) = 0.77 V versus SCE in acetonitrile, [26] E p/2 (methylene blue) = 1.60 V versus SCE in acetonitrile, [27] E p/2 (fluorescein) = 0.78 V versus SCE in acetonitrile, [28] E p/2 (rose bengal) = 0.99 V versus SCE in acetonitrile, [29] E p/2 (eosin Y) = 0.79 V versus SCE in acetonitrile]. [30] So, the above mentioned photocatalysts cannot react with substrate 1 a (E p/2 = 1.84 V versus SCE in acetonitrile) or 2 a (E p/2 = 1.81 V versus SCE in acetonitrile) via an electron transfer process.…”
Section: Resultsmentioning
confidence: 99%
“…In early 2020, Li and collaborators reported a methodology to incorporate difluoromethyl groups to quinoxalin-2-ones and other aromatic heterocycles. [51] The CF 2 H group is an important fluorinated functional group that, recently, have received huge attention in medicinal chemistry and pharmaceutical industry. This fluorinated group has been used as a lipophilic hydrogenbond donor, and as isoster of a thiol, a hydroxyl, and an amide, bringing new opportunities for drug development.…”
Section: Fluoroalkylation Reactionsmentioning
confidence: 99%
“…In early 2020, Li and collaborators reported a methodology to incorporate difluoromethyl groups to quinoxalin‐2‐ones and other aromatic heterocycles . The CF 2 H group is an important fluorinated functional group that, recently, have received huge attention in medicinal chemistry and pharmaceutical industry.…”
Section: C–c Bond Formationmentioning
confidence: 99%
“…In particular, photoredox catalysis using various organic photocatalysts is inexpensive and exhibits low toxicity. [1][2][3] However, photochemical organic transformations often occur at limited penetration distances due to the utilization of light through absorbing media. Consequently, the transformation e ciency may be low in conventional bulk reactors.…”
Section: Introductionmentioning
confidence: 99%
“…Co. Ltd., China) as an NIR light source. The solution of starting reagent (0.075 M) mixed with RB (5 mol%) in acetonitrile, reactant, and H 2 O (1:0.8:0.2 v/v/v) was fed into the fabricated micro uidic devices using a KD Scienti c Legato 180 syringe pump (Holliston, MA, USA) 1. H NMR (300, 400, or 500 MHz) and13 C NMR (125 MHz) spectra were recorded on a Bruker AVANCE III HD 300, 400 or 500-MHz NMR spectrometer in CDCl 3 .…”
mentioning
confidence: 99%